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Organic compound based on nitrogen-containing heterocyclic ring and preparation method and application of organic compound

A technology of organic compounds and nitrogen heterocycles, applied in the field of OLED materials, can solve the problems of low lifetime and low luminous efficiency, and achieve the effects of high structural regularity, high luminous efficiency, and high glass transition temperature

Inactive Publication Date: 2020-02-18
HEZE UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For commonly used anthracene-based fluorescent blue light materials, the luminous efficiency is low; for phosphorescent blue light materials such as Firpic, the lifetime is low

Method used

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  • Organic compound based on nitrogen-containing heterocyclic ring and preparation method and application of organic compound
  • Organic compound based on nitrogen-containing heterocyclic ring and preparation method and application of organic compound
  • Organic compound based on nitrogen-containing heterocyclic ring and preparation method and application of organic compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] The synthetic method of organic compound (1) is as follows:

[0034]

[0035] Compound 1-a (5g, 613.97g / mol, 8.14mmol), compound 1-b (2.1eq, 2.1g, 123.05g / mol, 17.1mmol) and sodium carbonate (4eq, 3.45g, 105.99g / mol, 32.57mmol) was added to a mixed solvent composed of toluene (100g, 20 times the mass of compound 1-a) and water (100g, 20 times the mass of compound 1-a), stirred and mixed and then added three (o-toluene Base) phosphine (5%eq, 0.12g, 304.37g / mol, 0.41mmol) and palladium (II) acetate (1%eq, 0.02g, 224.51g / mol, 0.08mmol), warming up to reflux and stirring for 10h, the reaction After finishing cooling to room temperature, filter, separate the toluene, extract the aqueous phase with toluene, combine the organic phases, wash with water, dry and then concentrate under reduced pressure to obtain the crude product, which is purified by column chromatography to obtain the organic compound (1) (4.04g , yield 81.1%), MS (EI): 613.2 (M+H) + .

Embodiment 2

[0037]

[0038] The synthetic method of organic compound (4) is as follows:

[0039]

[0040] Compound 2-a (5g, 916.11g / mol, 5.46mmol), compound 2-b (2.1eq, 1.41g, 123.05g / mol, 11.46mmol) and sodium carbonate (4eq, 2.31g, 105.99g / mol, 21.83mmol) was added to a mixed solvent composed of toluene (100g, 20 times the mass of compound 2-a) and water (100g, 20 times the mass of compound 2-a), stirred and mixed and then added three (o-tolyl) ) phosphine (5%eq, 0.08g, 304.37g / mol, 0.27mmol) and palladium (II) acetate (1%eq, 0.01g, 224.51g / mol, 0.05mmol), warming up to reflux and stirring for 15h, the reaction ended After cooling to room temperature, filter, separate the toluene, extract the aqueous phase with toluene, combine the organic phases, wash with water, dry and concentrate under reduced pressure to obtain the crude product, which is purified by column chromatography to obtain the organic compound (4) (3.87g, Yield 77.5%), MS (EI): 915.3 (M+H) + .

Embodiment 3

[0042]

[0043] The synthetic method of organic compound (15) is as follows:

[0044]

[0045] Compound 3-a (5g, 1200.27g / mol, 4.17mmol), compound 3-b (2.1eq, 1.08g, 123.05g / mol, 8.75mmol) and sodium carbonate (4eq, 1.77g, 105.99g / mol, 16.66mmol) was added into a mixed solvent composed of toluene (100g, 20 times the mass of compound 3-a) and water (100g, 20 times the mass of compound 3-a), stirred and mixed and then added three (o-tolyl) ) phosphine (5%eq, 0.06g, 304.37g / mol, 0.21mmol) and palladium (II) acetate (1%eq, 0.01g, 224.51g / mol, 0.04mmol), warming up to reflux and stirring for 15h, the reaction ended After cooling to room temperature, filter, separate the toluene, extract the aqueous phase with toluene, combine the organic phases, wash with water, dry and concentrate under reduced pressure to obtain the crude product, which is purified by column chromatography to obtain the organic compound (15) (3.71g, Yield 74.3%), MS (EI): 1199.5 (M+H) + .

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Abstract

The invention provides an organic compound based on a nitrogen-containing heterocyclic ring and a preparation method and application of the organic compound and relates to the field of OLED (organic light emitting diode) materials. The organic compound has a structural formula shown in the description. The organic compound provided by the invention has a high neat degree, high luminous efficiencyand heat stability, enables carrier transmission to be balanced, is applied to organic light emitting devices, especially used as a blue light emitting material in an OLDE light emitting layer, has high luminous efficiency, has a good application effect in OLED devices, has a good industrialization prospect.

Description

technical field [0001] The invention relates to the field of OLED materials, in particular to an organic compound based on a nitrogen-containing heterocycle and a preparation method and application thereof. Background technique [0002] Organic electroluminescence refers to the phenomenon that organic materials are excited by electric current and electric field to emit light under the action of electric field. Organic light-emitting diodes (OLEDs) are a next-generation display technology that utilizes this phenomenon to realize displays. Since Tang C.W. and Vanslyke S.A. of Kodak Company in the United States produced the first organic electroluminescent device with excellent performance in 1987, organic electroluminescent displays have attracted great interest due to their advantages. [0003] OLED has many advantages such as self-illumination, wide viewing angle, fast response speed, and flexible display, which makes it the most favorable competitor of the next-generation ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K11/06H01L51/50H01L51/54
CPCC07D487/04C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092H10K85/626H10K85/654H10K85/6574H10K85/6576H10K85/6572H10K50/11
Inventor 樊红莉李风海郭明晰郑蕾郭倩倩
Owner HEZE UNIV
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